메뉴 건너뛰기




Volumn 3, Issue 15, 2001, Pages 2269-2271

Stereoselective synthesis of chiral 2,3-cis-2-ethynylaziridines by base-mediated intramolecular amination of bromoallenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; AZIRIDINE DERIVATIVE; BROMINATED HYDROCARBON;

EID: 0035954878     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016027k     Document Type: Article
Times cited : (38)

References (42)
  • 23
    • 0025072488 scopus 로고
    • In limited cases, the reaction of metal acetylide with amino aldehydes proceeds in a highly stereoselective manner. For example, see: (a) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772.
    • (1990) J. Org. Chem. , vol.55 , pp. 3772
    • Garner, P.1    Park, J.M.2
  • 40
    • 0041619433 scopus 로고    scopus 로고
    • note
    • We observed isomerization of the 2,3-trans-2-ethynylaziridine 11b into the corresponding 2,3-cis-isomer 10b under the aziridination conditions (NaH, DMF, room temperature). Although a prolonged reaction time (> 10 h) was required for an efficient conversion (cis:trans = >95:5), equilibration of the products would be one of the important factors for the cis-selective aziridination. Thermodynamic preference of the related 2,3-cis-aziridines over their trans-isomers is well documented by our previous study; see: ref 2g.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.